2-Decarboxy-2-hydroxymethyl-17-phenyl-11-deoxy-PGF1 analogs

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 647,357, filed Jan. 8, 1976, now issued as U.S. Pat. No. 4,055,602.

The present invention relates to prostaglandin analogs, for which the essential material constituting disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,055,602, issued Oct. 25, 1977. 

I claim:
 1. A prostaglandin analog of the formula ##STR1## WHEREIN Y is trans--CH═CH--; wherein M₁ is ##STR2## wherein R₅ is hydrogen or methyl; WHEREIN L₁ is ##STR3## or a mixture of ##STR4## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is methyl only when the other is hydrogen or methyl;Wherein Z₂ is Cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --; cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂ --; or --(CH₂)₃ --(CH₂)_(g) --CF₂ --; wherein g is one, 2, or 3; and Wherein s is zero, one, 2, or 3 and T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, the various T's being the same or different, with the proviso that not more than two T's are other than alkyl.
 2. A compound according to claim 1, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
 3. A compound according to claim 2, wherein Z₂ is cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --.
 4. A compound according to claim 3, wherein g is one.
 5. A compound according to claim 4, wherein at least one of R₃ and R₄ is fluoro.
 6. A compound according to claim 5, wherein R₃ and R₄ are both fluoro.
 7. A compound according to claim 6, wherein R₅ is methyl.
 8. 2-Decarboxy-2-hydroxymethyl-2,2,16,16-tetrafluoro-15-methyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₂ α, a compound according to claim
 7. 9. A compound according to claim 6, wherein R₅ is hydrogen.
 10. 2-Decarboxy-2-hydroxymethyl-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-11-deoxy-PGF₂ α, a compound according to claim
 9. 11. A compound according to claim 4, wherein at least one of R₃ and R₄ is methyl.
 12. A compound according to claim 11, wherein R₃ and R₄ are both methyl.
 13. A compound according to claim 12, wherein R₅ is methyl.
 14. 2-Decarboxy-2-hydroxymethyl-2,2-difluoro-15,16,16-trimethyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₂ α, a compound according to claim
 13. 15. A compound according to claim 12, wherein R₅ is hydrogen.
 16. 2-Decarboxy-2-hydroxymethyl-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₂ α, a compound according to claim
 15. 17. A compound according to claim 4, wherein R₃ and R₄ are both hydrogen.
 18. A compound according to claim 17, wherein R₅ is hydrogen.
 19. 2-Decarboxy-2-hydroxymethyl-2,2-difluoro-15-methyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₂ α, a compound according to claim
 18. 20. A compound according to claim 17, wherein R₅ is hydrogen.
 21. 2-Decarboxy-2-hydroxymethyl-2,2-difluoro-17-phenyl-18,19,20-trinor-11-deoxy-PGF₂ α, a compound according to claim
 20. 22. A compound according to claim 2, wherein Z₂ is --(CH₂)₃ --(CH₂)_(g) --CF₂ --.
 23. A compound according to claim 22, wherein g is one.
 24. A compound according to claim 23, wherein at least one of R₃ and R₄ is fluoro.
 25. A compound according to claim 24, wherein R₃ and R₄ are both fluoro.
 26. A compound according to claim 25, wherein R₅ is methyl.
 27. 2-Decarboxy-2-hydroxymethyl-2,2,16,16-tetrafluoro-15-methyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF.sub. 1 α, a compound according to claim
 26. 28. A compound according to claim 25, wherein R₅ is hydrogen.
 29. 2-Decarboxy-2-hydroxymethyl-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 28. 30. A compound according to claim 23, wherein at least one of R₃ and R₄ is methyl.
 31. A compound according to claim 30, wherein R₃ and R₄ are both methyl.
 32. A compound according to claim 31, wherein R₅ is methyl.
 33. 2-Decarboxy-2-hydroxymethyl-2,2-difluoro-15,16,16-trimethyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 32. 34. A compound according to claim 31, wherein R₅ is hydrogen.
 35. 2-Decarboxy-2-hydroxymethyl-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 34. 36. A compound according to claim 23, wherein R₃ and R₄ are both hydrogen.
 37. A compound according to claim 36, wherein R₅ is methyl.
 38. 2-Decarboxy-2-hydroxymethyl-2,2-difluoro-15-methyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 37. 39. A compound according to claim 36, wherein R₅ is hydrogen.
 40. 2-Decarboxy-2-hydroxymethyl-2,2-difluoro-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 39. 41. A compound according to claim 2, wherein Z₂ is cis-CH₂ --CH═CH--(CH₂)_(g) --CH₂ --.
 42. A compound according to claim 41, wherein g is one.
 43. A compound according to claim 42, wherein at least one of R₃ and R₄ is fluoro.
 44. A compound according to claim 43, wherein R₃ and R₄ are both fluoro.
 45. A compound according to claim 44, wherein R₅ is methyl.
 46. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-methyl-16,16-difluoro-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 45. 47. A compound according to claim 44, wherein R₅ is hydrogen.
 48. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-difluoro-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 47. 49. A compound according to claim 42, wherein at least one of R₃ and R₄ is methyl.
 50. A compound according to claim 49, wherein R₃ and R₄ are both methyl.
 51. A compound according to claim 50, wherein R₅ is methyl.
 52. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15,16,16-trimethyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 51. 53. A compound according to claim 50, wherein R₅ is hydrogen.
 54. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-dimethyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 53. 55. A compound according to claim 42, wherein R₃ and R₄ are both hydrogen.
 56. A compound according to claim 55, wherein R₅ is methyl.
 57. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-methyl-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 56. 58. A compound according to claim 55, wherein R₅ is hydrogen.
 59. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-17-phenyl-18,19,20-trinor-11-deoxy-PGF₁ α, a compound according to claim
 58. 